Bailey was born in India where his father worked on the railways. When he was four, his family returned to London where his father found at a job at the Victoria & Albert Museum. Fascinated by the collections in the museum, Bailey began to draw.
Study and work
Bailey studied illustration at Brighton Art School, where he met his future wife, Sian. After working as a freelance artist for five years, he took a teaching position at the Liverpool art school. In 1997, Bailey left his job and became a full-time illustrator.